In Cloudberry Kingdom, the player takes the role of the retired hero Bob. As the princess is kidnapped once again by King Kobbler with his magic orb, he has to save her. Again. The story is told in humorous cutscenes, but does play a negligible role. More important are the randomly generated levels which take the player's skill in previous levels and chosen difficulty level into account - in principle the campaign is designed to be always challenging.
Gameplay itself is platforming standard: Bob walks and jumps from left to right while avoiding all kinds of obstacles. Some enemies can be destroyed by jumping on them and the level can be directly restarted after dying; there is no game over. In some levels there is auto-scrolling or Bob receives gimmick abilities like a jet-pack or he constantly grows and shrinks. Of course the levels are generated to account for the ability. The player always can activate a help option where an AI character shows how to beat the level - but it has to be bought with crystals which can be collected during the levels.
Besides the campaign, players can also engage in free play (all parameters of level creation can be freely adjusted), Time Crisis (players are on a time limit which has to be expanded by collecting crystals), Hero Rush (randomly assigns gimmick abilities) and Hybrid Rush (like Hero Rush, just sometimes with multiple abilities at once). Each mode, including the campaign, can be also played in co-op. An even bigger challenge is the bungee mode in which players are connected with a bungee cord.